US12239151B2 - 2-acetylpyrroline precursor - Google Patents

2-acetylpyrroline precursor Download PDF

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US12239151B2
US12239151B2 US17/621,825 US202017621825A US12239151B2 US 12239151 B2 US12239151 B2 US 12239151B2 US 202017621825 A US202017621825 A US 202017621825A US 12239151 B2 US12239151 B2 US 12239151B2
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products
drinks
beverages
flavored
acetylpyrrolidin
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US20220361542A1 (en
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Christian Starkenmann
Yvan Niclass
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Firmenich SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/205—Heterocyclic compounds
    • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to the field of flavor. More particularly, it concerns a precursor compound of formula (I) releasing 2-acetyl-1-pyrroline and a method to release 2-acetyl-1-pyrroline from the precursor compound of formula (I). Moreover, the present invention relates to a flavoring composition and a flavored consumer product comprising at least one compound of formula (I).
  • 2-acetyl-1-pyrroline (2-AP) was identified as the principal aroma compound responsible for the pleasant aroma in scented rice while possessing a bread, nutty, popcorn and basmati notes.
  • 2-AP 2-acetyl-1-pyrroline
  • the scope of 2-AP expands beyond rice as it reveals its presence in a large variety of living systems and food products and imparts organoleptic impression needed in a large amount of flavored article.
  • 2-AP is highly unstable due to the pyrroline ring rendering the use of said compound in flavored article very difficult.
  • the present invention provides new compounds able to release 2-AP to improve the consumer experience under certain triggers.
  • the precursor compound of formula (I) allows stabilizing 2-acetyl-1-pyrroline by releasing it when needed in the consumer product article.
  • the present invention's allows to improve the organoleptic impact of 2-acetyl-1-pyrroline by avoiding premature decomposition in flavoring compositions or flavored consumer products.
  • the first object of the present invention is method to release 2-acetyl-1-pyrroline from a precursor compound of formula
  • R 1 represents a hydrogen atom or a C 1 to C 10 hydrocarbon group optionally comprising one to three heteroatoms
  • X represents an amino acid, a peptide, a carbohydrate moiety or a OR 2 wherein R 2 represents a hydrogen atom or a C 1 to C 20 hydrocarbon group optionally comprising one to three heteroatoms and n is 0 when the dotted line represents a single bond or n is 1 when the dotted line represents no bond; comprising treating the precursor compound to form 2-acetyl-1-pyrroline.
  • a second object of the present invention is use of a compound of formula (I) as defined above to release 2-acetyl-1-pyrrolidine.
  • a third object of the present invention is method to confer, enhance, improve or modify the flavor properties of a flavoring composition or of a flavored article, comprising adding to the composition or article an effective amount of at least one compound of formula (I) as defined above.
  • Another object of the present invention is a method for intensifying or prolonging the diffusion effect of the characteristic flavor of 2-acetyl-1-pyrrolidine by exposing the precursor compound of formula (I) as define above to a temperature above 30° C.
  • Another object of the present invention is a compound of formula
  • Another object of the present invention is a flavoring composition
  • a flavoring composition comprising:
  • FIG. 1 Analysis of the concentration of 2-acetylpyrroline in function of time.
  • the first object of the present invention is a method to release 2-acetyl-1-pyrroline from a precursor compound of formula
  • Said method comprises treating the precursor compound to form 2-acetyl-1-pyrroline.
  • any one of its stereoisomers or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the invention compound can be a pure or be in the form of a mixture of enantiomers or diastereomers.
  • tautomers or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the ketone may be in a form of an enol.
  • salts or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that compound of formula (I) in presence of an acid such as HCl, sulfuric acid, phosphoric acid or hydrogeno sulfates, reacts with said acid to form the corresponding salt.
  • an acid such as HCl, sulfuric acid, phosphoric acid or hydrogeno sulfates
  • amino acid it is meant the normal meaning in the art; i.e. a compound having a carboxylic functional group and an amine functional group.
  • the amino acid may be natural or synthetic.
  • the amino acid may be a natural alpha amino acid.
  • peptide designates compound composed of at least two amino acids connected by peptide bonds.
  • the peptides may be an oligopeptide comprising from 2 to twenty amino acids or a polypeptides comprising more than twenty peptides.
  • a carbohydrate moiety or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. a monosaccharide, an oligosaccharide or a polysaccharide.
  • hydrocarbon group is understood as a group consisting of hydrogen and carbon atoms and can be in the form of an aliphatic hydrocarbon, i.e. linear or branched saturated hydrocarbon (e.g. alkyl group), a linear or branched unsaturated hydrocarbon (e.g. alkenyl or alkynyl group), a saturated cyclic hydrocarbon (e.g. cycloalkyl) or an unsaturated cyclic hydrocarbon (e.g. cycloalkenyl or cycloalkynyl), or can be in the form of an aromatic hydrocarbon, i.e. aryl group, or can also be in the form of a mixture of the type of groups, e.g.
  • a specific group may comprise a linear alkyl, a branched alkenyl (e.g. having one or more carbon-carbon double bonds), a (poly)cycloalkyl and an aryl moiety, unless a specific limitation to only one type is mentioned.
  • a group when a group is mentioned as being in the form of more than one type of topology (e.g. linear, cyclic or branched) and/or being saturated or unsaturated (e.g. alkyl, aromatic or alkenyl), it is also meant a group which may comprise moieties having any one of the topologies or being saturated or unsaturated, as explained above.
  • a group when a group is mentioned as being in the form of one type of saturation or unsaturation, (e.g. alkyl), it is meant that the group can be in any type of topology (e.g. linear, cyclic or branched) or having several moieties with various topologies.
  • the hydrocarbon group when it is mentioned that the hydrocarbon group may optionally comprises heteroatom such as oxygen atoms, nitrogen atoms or sulphur atoms, it is meant that at least one hydrogen atom of the hydrocarbon group may be substituted by a heteroatom and/or that carbon atom of the hydrocarbon chain may be substituted/replaced by a heteroatom; i.e. the hydrocarbon may comprise as substituent or, as part of the chain, functional group such as ether, thiol, amine, ester, amide.
  • the precursor compound is a compound of formula (I′).
  • n is 0 and the dotted line is a single bond.
  • X may represent a OR 2 wherein R 2 represents a hydrogen atom or a C 1 to C 20 hydrocarbon group optionally comprising one to three heteroatoms.
  • the precursor compound is of formula
  • R 1 may represent a hydrogen atom or a C 1 to C 10 hydrocarbon group optionally comprising one to three oxygen, nitrogen or sulfur atoms.
  • R 1 may represent a hydrogen atom or a C 1 to C 4 alkyl group optionally substituted by a carboxylic acid, an amide, a thiol, a C 1-3 thioether, an amine, a hydroxyl, an imidazolyl, and indolyl, a phenyl or a hydroxyphenyl group.
  • R 1 may represent a hydrogen atom, a C 1 to C 3 alkyl group optionally substituted by a carboxylic acid or a phenyl group.
  • R 1 may represent a hydrogen atom, a methyl group, an ethyl group, a propyl group, an isopropyl group, a (CH 2 ) p COOH group wherein p is 1 or 2 or a benzyl group.
  • R 1 may represent a hydrogen atom, a methyl group, a (CH 2 ) p COOH group wherein p is 1 or 2 or a benzyl group.
  • R 1 may represent a hydrogen atom, a methyl group or a (CH 2 ) p COOH group wherein p is 1 or 2. Even more preferably, R 1 may represent a hydrogen atom or a methyl group.
  • R 2 may represent a hydrogen atom or C 1 to C 10 hydrocarbon group optionally comprising one to three oxygen, nitrogen, sulfur or halogen atoms.
  • R 2 may represent a hydrogen atom or C 1 to C 6 hydrocarbon group optionally comprising one to three oxygen, nitrogen or sulfur atoms.
  • R 2 may represent a hydrogen atom or a C 1 to C 3 hydrocarbon group.
  • R 2 may represent a hydrogen atom or a C 1 to C 3 alkyl group.
  • R 2 may represent a hydrogen atom or a C 1 to C 3 linear alkyl group. Even more preferably, R 2 may represent a hydrogen atom.
  • said compounds (I) are C 8 -C 23 compounds, preferably C 8 -C 15 compounds.
  • the precursor compound may be selected from the group consisting of (4-hydroxy-5-oxohexyl)glycine, 2-(2-acetylpyrrolidin-1-yl)acetic acid, (4-hydroxy-5-oxohexyl)alanine, 2-(2-acetylpyrrolidin-1-yl)propionic acid, methyl (4-hydroxy-5-oxohexyl)alaninate, methyl 2-(2-acetylpyrrolidin-1-yl)propanoate, (4-hydroxy-5-oxohexyl)phenylalanine, 2-(2-acetylpyrrolidin-1-yl)-3-phenylpropanoic acid, (4-hydroxy-5-oxohexyl)aspartic acid, 2-(2-acetylpyrrolidin-1-yl)succinic acid, (4-hydroxy-5-oxohexyl)glutamic acid and 2-(2-acetylpyrrolidin
  • the precursor compound may be selected from the group consisting of 2-(2-acetylpyrrolidin-1-yl)acetic acid, 2-(2-acetylpyrrolidin-1-yl)propionic acid, methyl 2-(2-acetylpyrrolidin-1-yl)propanoate, 2-(2-acetylpyrrolidin-1-yl)-3-phenylpropanoic acid, 2-(2-acetylpyrrolidin-1-yl)succinic acid and 2-(2-acetylpyrrolidin-1-yl)-5-oxohexanoic acid.
  • the release of 2-acetyl-1-pyrrolidine occurs by exposing the precursor compound to a temperature above 30° C., even more, above 50° C., even more, above 60° C., even more, above 70° C., even more, above 80° C., even more, above 90° C.
  • Another object of the present invention is a method for intensifying or prolonging the diffusion effect of the characteristic flavor of 2-acetyl-1-pyrrolidine by exposing the precursor compound of formula (I) as define above to a temperature above 30° C. even more, above 50° C., even more, above 60° C., even more, above 70° C., even more, above 80° C., even more, above 90° C.
  • Another object of the present invention is the use of a compound of formula (I) as defined above to release 2-acetyl-1-pyrrolidine.
  • it concerns confer, enhance, improve or modify the flavor properties of a flavoring composition or of a flavored article, comprising adding to the composition or article an effective amount of at least one compound of formula (I) as defined above, e.g. to impart its typical note.
  • the final hedonic effect may depend on the precise dosage and on the organoleptic properties of the invention's compound, but anyway the addition of the invention's compound will impart to the final product its typical touch in the form of a note, touch or aspect depending on the dosage.
  • compositions which in fact can be advantageously employed as flavoring ingredients, are also an object of the present invention.
  • the present invention also relates to a flavoring composition
  • a flavoring composition comprising:
  • flavor carrier designates a material which is substantially neutral from a flavor point of view, insofar as it does not significantly alter the organoleptic properties of flavoring ingredients.
  • the carrier may be a liquid or a solid.
  • Suitable liquid carriers include, for instance, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in flavors.
  • an emulsifying system i.e. a solvent and a surfactant system
  • a solvent commonly used in flavors A detailed description of the nature and type of solvents commonly used in flavor cannot be exhaustive.
  • Suitable solvents used in flavor include, for instance, propylene glycol, triacetine, caprylic/capric triglyceride (Neobee®), triethyl citrate, benzylic alcohol, ethanol, vegetable oils such as Linseed oil, sunflower oil or coconut oil, glycerol
  • Suitable solid carriers include, for instance, absorbing gums or polymers, or even encapsulating materials.
  • materials may comprise wall-forming and plasticizing materials, such as mono, di- or polysaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, xanthan gum, arabic gum, acacia gum or yet the materials cited in reference texts such as H. Scherz, Hydrokolloid: Stabilisatoren, Dickungs- and Gelierstoff in Strukturn, Band 2 der Kunststoffen Herbert Strukturchemie, claritat, Behr's VerlagGmbH & Co., Hamburg, 1996.
  • Encapsulation is a well-known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration, extrusion, coating, plating, coacervation and the like.
  • flavoring or perfuming co-ingredient it is meant here a compound, which is used in flavoring or perfuming preparations or compositions to impart a hedonic effect.
  • an ingredient to be considered as being a flavoring or perfuming one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the taste or the odor of a composition, and not just as having a taste or an odor.
  • flavoring or perfuming co-ingredients present in the composition do not warrant a more detailed description here, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
  • these flavoring or perfuming co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said flavoring or perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
  • flavor adjuvant an ingredient capable of imparting additional added benefit such as a color (e.g. caramel), chemical stability, and so on.
  • a color e.g. caramel
  • chemical stability e.g. a detailed description of the nature and type of adjuvant commonly used in flavoring compositions cannot be exhaustive. Nevertheless, such adjuvants are well known to a person skilled in the art who will be able to select them on the basis of its general knowledge and according to intended use or application.
  • viscosity agents e.g. emulsifier, thickeners, gelling and/or rheology modifiers, e.g. pectin or agar gum
  • stabilizing agents e.g. antioxidant, heat/light and or buffers agents e.g. citric acid
  • coloring agents e.g. natural or synthetic or natural extract imparting color
  • preservatives e.g. antibacterial or antimicrobial or antifungal agents, e.g. benzoic acid
  • vitamins and mixtures thereof e.
  • the flavored composition may further comprise ingredient imparting a warming, a tingling, a salivating, a cleaning or an alcohol enhancement effect such as capsicum extract, spice extract (e.g. ginger, maniguette, all types of peppers including Sichuan, piperine, capsaicine, jambu extract, spilanthol.
  • any mixture resulting directly from a chemical synthesis e.g. a reaction medium without an adequate purification, in which the compounds of the invention would be involved as a starting, intermediate or end-product could not be considered as a flavoring or perfuming composition according to the invention as far as said mixture does not provide the inventive compound in a suitable form for perfumery or for flavor.
  • unpurified reaction mixtures are generally excluded from the present invention unless otherwise specified.
  • a composition consisting of at least one invention's precursor and at least one flavor carrier represents a particular embodiment of the invention as well as a flavoring composition comprising at least one invention's precursor, at least one flavor carrier, at least one flavor co-ingredient, and optionally at least one flavor adjuvant.
  • Typical examples of said flavored consumer product include:
  • the flavored consumer product may be baked goods, dairy based products, dairy analogues, products based on fat and oil or emulsions thereof, milk products, confectionary products, desserts, chocolate and compound coatings, cereal products, non-alcoholic beverages, alcoholic beverages or instant or ready-to-drink beverages.
  • the flavored consumer product may be covertures and filling, products based on sugars, breads, dry biscuits, cakes, rice cakes, rice crackers, cookies, crackers, donuts, muffins, pastries, pre-mixes, filings, toppings, fruit or flavored yoghurts, ice creams, fruit ices, frozen desserts, spreads, regular or low fat margarines, butter/margarine blends, flavored oils, shortenings, dressings, spice preparations, peanut butters, fresh cheeses, soft cheeses, milk drinks, wheys, butters, partially or wholly hydrolysed milk protein-containing products, fermented milk products, condensed milk and analogues, gelatins, puddings, dessert creams, chocolates, spreads, aqueous beverages, enhanced/slightly sweetened water drinks, flavored carbonated and still mineral and table waters, carbonated soft drinks, non-carbonated beverages, carbonated waters, still waters, softs, bottled waters, sports/energy drinks, juice drinks,
  • Some of the above-mentioned flavored consumer products may represent an aggressive medium for the invention's precursor, so that it may be necessary to protect the invention's composition from premature decomposition, for example by encapsulation.
  • the pH of the consumer product in which the invention's precursor is introduced is neutral.
  • the invention's precursor can be prepared according to standard method known in the art as described herein-below or may be extracted from plant comprising such an extract as Chinese lettuce.
  • the invention's precursor may also be in a form of an extract, in particular in a form of a Chinese lettuce extract.
  • the Liquid chromatography mass spectrometry were recorded on a Thermo ScientificTM VanquishTM UHPLC.
  • the mass spectrometer Thermo ScientificTM Q ExactiveTM Basic Mass Spectrometer.
  • a column was an Acquity UPLC BEH C18 1.7 um. 2.1 mm internal diameter ⁇ 100 mm. Eluent was water/formic acid 0.1% 100% at 0 min to 1 min. then from 1 min 0% to 100% acetonitrile containing 0.1% formic acid at 0.3 mL/min.
  • Another column was Acquity UPLC BEH Amide 1.7 um. 2.1 mm, internal diameter ⁇ 100 mm.
  • This column was operated with a buffer: solvent A: water/acetonitrile 1/1 containing ammonium formiat 10 mM and formic acid 0.02%, solvent B: water/acetonitrile 1/9 containing ammonium formiat 10 mM and formic acid 0.02% at 0.6 mL 7 min. Gradient started at 100% B for 1 min. then to 85% B in 5 min, to 50% B in 4 min, 20% B in 2 min 0% B in 1 min, then back to 100% B in one min. total run 14 min. This column was also operated in formic acid at 0.3 mL/min flow rate. Solvent A: water containing 0.1% formic acid; solvent B: acetonitrile containing 0.1% formic acid.
  • MS had targeted SIM in positive mode, with an isolation window of 4.0 m/z and a resolution of 70′000 and max IT of 200 ms.
  • PRM with a resolution of 17′500, max IT 60 ms, isolation window 1.0 m/z and the collision energy 10, 30, 45 was automatically set.
  • the inclusion list was: 172.0967, 190.1072, 186.1124, 204.1228, 230.1021, 248.1127, 244.1178, 262.1284.
  • a calibrations curve was done with water (6 mL), 10 ⁇ L of toluene and lutidine (50 ⁇ L of a solution 1 mg/mL EtOH), then vial 1 to 4 contained respectively, instead of toluene, 2-AP in toluene, respectively 10 ⁇ L of 50, 100, 500, 1000 ⁇ g/mL. All measurements were made in triplicate.
  • the SPME conditions were: 5 min. conditioning at 270° C., the exposure was 3 min after having heated the sample at 120° C. during 15 min and then 60 min. The thermo-desorption, in split less mode, was 1.5 min at 250° C.
  • the quantification was performed in full MS based on the intensity ratio in extract ion mode: 111 (2-AP)/107 (lutidine).
  • the pH was in any case between 6.5-7.0.
  • the standard error was ⁇ 16%.

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EP3962893A1 (de) 2022-03-09
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